Joanne Falla decided she needed to go bigger: a bigger house and a bigger boat. Her home in Harwich on Cape Cod, Mass., wasn’t big enough for her close-knit family—a father, two sisters, a brother-in-law, a nephew and a dog—to gather. Since the start of the lockdown, the 51-year-old Boston-based tech executive was living and working in the 1789 building that was her father’s law office for 30 years. She wanted a home in the area that she could share with her 80-year-old father, Jim, and with the entire family for vacations and weekends.